He's applied that same appetite for risk along with a "try-try-again" attitude when he made the leap from pro sports to retail, wholesale and then retail again. According to him, "failing will create your next opportunity."

Some of those risks have paid off. HUF is now a global streetwear brand, recently infused with capital to grow even bigger. Some of his risks have even skated legal limits-- you could wallpaper HUF's warehouse with the amount of cease and desist letters he's gotten for pushing the "let's do crazy shit" button.

In our conversation, HUF talks about risk and what it's taken for him to stay focused and keep trying again--even when he's fallen down a lot. The take-away? You have to eat a lot of shit to get somewhere. HUF would know.